Dating at Midlife/Oh wow.....


QUESTION: Well this is something I have never encountered in all my years of being divorced and dating.  I have been dating a guy just under a year now that is probably the most amazing man I have ever been with.  Sweet, generous, kind, truly treats me with such kindness, love and respect.  He is honestly one of those guys that you would never have to worry about his lying to you, or cheating on you.   Something I can honestly say I haven't experienced before as my ex husband and a couple of the guys I have dated in the past were proficient at both.

That said, what seems to be the problem with him then you might ask?

Well after being together now for several months I have just learned that he is financially broke.  And I mean it seems big time in debt.  

We have begun talking about marriage.  Just in passing conversation, not specific plans as yet.  But enough that yesterday he decided that we needed to talk about his situation.  He works commission only on boat sales and the market for sales has been slow for so long that he is literally just loping along. Apparently he has lived off credit cards and what bit of money he gets from other ventures.

Also, his divorce hit him pretty hard financially.  Appears that his arrangements for his house is that his ex wife is still on the house even though they have been divorced for several years.  Should something happen to him, the house apparently goes to her.

And, he hasn't paid the last couple of years of taxes.

When he first told me all of this, I really didn't say much.  Wasn't sure what I could say.  We haven't been dating for years so I kind of felt that while I appreciated his being upfront with me, at the same time I didn't feel I have much right to say anything about it.

Now, there is another caveat to all of this.  I found out that he is such a generous man, that even though he is basically broke since he is a nice man several of his friends ask him for monetary help.  A woman he works with is facing surgery with no insurance.  She comes to him and he helps her as best he can.  She couldn't pay her rent a time or two, so he gave her rent.  A guy he knows got into some trouble and needed rent money.  He gave him rent money.  This is one of the areas where I have felt I have no say so.  We are not married so technically what he does with what little money he gets is his business.  HOWEVER, what just kills me is that he is having to use credit cards to live while he gives money to others.  And they know he is stretched himself, but it doesn't matter they still tell him their woes and hold out their hand.

My past history is dating men that have high paying jobs and they spent freely and that included on me.  However, those free spending generous VP types were cheaters and liars and I spent the majority of my time looking good and traveling the world while always wondering who they were going to bed behind my back.  Or what emails they were writing to flirt with other women.

This guy.... he has never once told me no on anything and he takes me out to nice dinners, movies etc.  And more importantly is the kind that when I have a bad day, he brings me frozen yogurt and sits with me while I just cry if that is what I need to do.  He is the kind that when I get home has my favorite drink in a cold glass waiting on me.  And is the kind of guy that I can trust with my heart and never worry what he is doing behind my back.

So.... I keep telling myself that his financial situation is nothing for me to worry about.  That it is something we can work through.  That how he treats me is all that matters.  But down deep it scares the hell out of me.  I am loving every minute with him, but I find myself afraid of taking any steps toward marriage because I am scared of taking on his debt, the IRS coming and arresting him for not paying his taxes, and afraid of his generosity to others in need when he isn't taking care of his financial needs first.

I can see a life with him the man, but I hate to say that his financial situation really does scare me.  I have many years yet to work, but I hope not to have to work forever and I worry about what it would be like to be the main income for us.

How do you move forward with someone like that, however, not just ignore what is in front of you?


This is not an unusual problem, unfortunately.  
There are several aspects.
The general situation
His situation
Your situation

The "trickle down economy"/no socialism/ etc  concept has been in place inthe U.S. for a couple of decades and a lot of middle class folks aren't middle class anymore and probably aren't going to be for a long time, if ever. An unbelieva ble amount of money has been sucked upwards by "trickle down."  And so the problem is very common.  Folks don't like to talk. They are ashamed. Here is another question just this month. YOu can read it and feel less alone  
it was one of the last three or so questions I answered.

His situation:
In it I said that money issues for men are very difficult, sort of the way body issues are for women.
I guess I could say that men live beyond their means the way some women get breast implants and botox.  
It's hard times.

I've also said that one should never have only one theory about someone else's motives and so I can o nly make guesses about him from a distance. But it does seem that there is some shame  about being broke.

And he's a good hearted guy, too. Sounds practicaly saintly.

So maybe a little dysfuncdtional around this issue, too.
I say "dysfunctional" because he's in a lot of trouble.
I say "shame" because he was with you a long time before telling you his secret.

Your situation:
You are going to have to do what he could not do.
You will have to be a model for him and you will have to set a standard for
values and policies in the relationship you are considering creating with him.
(I might add that it is not unusual for women to need to be extremely practical when
they are married to men who are extremely idealistic.)
As they say whenthe plane takes off, if you are traveling with someone
when the oxygen masks drop down, and they need your help
You simply cannot connect yourself to someone with that financial
positions and that management policy.
So you have to speak to this.
The question is whether he declares bankruptsy while you are at a safe
distance, and whether he can,
whether the two of you establish policies for addressing these issues constructively.
And if you cannot,
the relationshp has to end. Or you go down with him.

THis will be a great shock to him. But he probably needs it.

Feel free to follow up

Phililp Alan Belove. Ed.D.

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QUESTION: It has been a few days since our first communication on this and I discovered something today that is making this even more shocking to me.  And I am working through my mind what my next steps are.

I just learned that the man that I referenced my SO helped has hit him up over the last year or so to the tune of more than 30,000.00.  I am just blown away.

As I told you the guy I am dating is such a kind and generous person, and that is one of his endearing qualities. BUT THIS KIND OF GENEROSITY JUST SIMPLY BOARDERS ON NAIVETE, OR STUPIDITY!  If my guy was wealthy and that was walking around money I could perhaps be more generous of heart.  But he is struggling to make his own bills, pay his taxes and living pay check to pay check.  He doesn't have that kind of money!!

The guy he is helping I believe is truly just using and abusing him.  Every time he asks for money he tell him that it is the "last time", that he will pay him back etc.  And he just recently ended up in jail.  He sends him letters begging him for money, sends him texts, calls constantly etc.  Dr. Belove, my guy keeps saying that this guy has a pending lawsuit (according to the jailbird) and once the lawsuit is settled he will pay him back.  My SO is going on faith that the guy is telling him the truth, yet knows that he could be lying and he will never recoup the money.  YET he just gave him more money this week!!!!!!

I am totally wigging out about this YET it isn't my immediate problem.  I am not married to him, what he does with his money is his business... yada yada yada (that is what I keep telling myself)

HOWEVER, where it becomes my business is that I CAN NOT make a future with a man that gives away money that he simply doesn't have and is in huge amount of debt of his own.  I just don't understand the concept of giving away the money you have when you can't even pay your own bills.  I feel like he has made himself the target of all kinds of people in "need" and he just has no idea how to say NO and take care of himself.

Dr. Belove, we have talked about marriage.  We have talked about his debt, and he has told me it is quite large, but given no specifics of just how large.  

In the first months of this relationship I wasn't comfortable approaching the topic as I truly felt it was not my business.  Now that we have been dating for this long and talking about a future together, one that seems to hinge on the fact that he is not financially in a position to marry me I feel compelled to speak up.  And... I know you said in your earlier response that it would come to that.

Now that I know this amount of money is owed to him and he is still throwing good money after bad, I feel very strongly that the discussion has to happen.

WHY WOULD SOMEONE DO THIS??  Why would he give money to someone he hardly knows, someone that he isn't related to, someone that is doing nothing to better himself but rather continuing to hold his hand out and it be to the detriment of his own well being??   What would propel a man to cause himself financial harm trying to help someone else?

In the past I have been with him a couple of times when the guy called asking for money and we had to run to the bank/store and get a moneygram sent.  At this stage in the game I am compelled to say that the next time it happens I want to refuse to go with him telling him that going with him says I support his doing that, and that given what it is doing to him and long range to my ability to have a relationship with him I can't/won't do it.  Is that appropriate?

I also feel that I need to have a candid talk with him telling him that while I do love him with all my heart, and do hope for a future with him, I can't plan for a future with someone that is being financial irresponsible by giving his money away like that when he isn't able to pay his own bills.   And that there will come a point when if I can't plan a future with him, I will have to leave the relationship to seek opportunities with someone that I can have that with.   Is that on the right track?

And at what point is it appropriate to have this kind of conversation.  I struggle with the fact that one minute I feel this length of time is long enough, and then there are times I feel that it isn't since it has just been under a year.

OMG.... what to do???

Good questions. When do you do this?  Is it too soon?

Well, the measure is your internal sense
Your emotional instrument panel is going all fourth of july.
A lot of alarm bells going off.

We just can't ignore those promptings.  Never. Never in any relationship.
If we try they just get louder.

Now this questions of whether the time is long enough
gets settled this way.
not enough time because the relationship is too short
you say nothing and just walk away.
A little longer, a vague answer because
there is no negotiating and you don't want a conversation.

A little longer than that and a great affection for the person,
then you give a real explanation. You apologize but still go.

A little longer than that, you give an ultimatum.  This has to change
or its' over.

Finally, after several conversations (no more than 3) you say, Sorry.
You're a wonderful person but we can't be in an intimate relationship
I can't have my life connected to that kind of risky behavior. Good bye.

If there is promise of change you need to see a concrete plan and you need real information.
and a timetable. And then you still might go if the plan is unacceptable or not followed.
Essentially that;s a commitment to a lot of work done for love.

That's a bunch of rules of thumb.

If I hear this right, you're going between ultimatum and
And you do like him so you owe him a conversation.

Also , if  he loses this relationship maybe it will be a wake up call. Maybe you
do him a favor.

I don't think this is negotiable at this point.
I suspect you won't get the truth out of him.

My hunch is that you say, in effect,
I love you but your train is going over a cliff and
you're not doing anything about it
nd I can't be on that train with you.

Let me know.

Philip Alan Belove, Ed.D.  

Dating at Midlife

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Philip Belove, Ed.D.


Hi. I`m Philip Belove (that is my name, really). I`m 71 and I`ve been a psychologist all my midlife, the past 35 years. My specialty has been counseling and coaching other midlife adults.  I think we all figure things out as we go along, but even more so at midlife. Being between 40-ish and 60-ish and single is like being a stranger in a strange land. I`ve learned which questions help people find their own way. I created this category, I publish a blog at and I write articles for various web sites. My commitment is to help people 1) understand and improve how they deal with others, 2) understand the forces that rule the relationships they are in, and 3) make the decisions which will shape, or create, or end those relationships  so they achieve the goal of midlife development  to finally live with personal satisfaction. I`ve been divorced twice myself. I`m in a satisfying relationship with a fine person. I`m very interested in learning about your challenges and in offering what I can.


Professionally: Licensed Psychologist. Marriage and Family Therapist. Coach.Author. University Lecturer. Personally: I'm 71. I've probably made all the big mistakes, er, learned the big lessons.I've forgiven myself and made many apologies and I've made it into a good, stable, sweet relationship. I now have a perspective on midlife.

Please check out my book, Rabbis in Love, at Also my blog at The Rabbi book was done as part of a research project. My collaborator, Marilyn Bronstein, and I wanted to interview couples with very successful marriage and also we wanted to talk to people who cared as much about their spirituality as love. Maybe being able to love and be spiritual were one and same, we thought. So we found a rabbi couple and the interview was so astounding that we interviewed nine more rabbi couples. One dropped. They'd revealed too much. It's a fascinating book and, Jewish or not, religious or not, these couples do a lot of things right and there is a lot to learn from them.

Masters in Counseling Psychology, Alfred Adler Institute Doctorate in Consulting Psychology, focus on family therapy, University of Massachusetts at Amherst

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